Reaction of Isolated Double Bonds with Selenium Dioxide/Hydrogen Peroxide: Formation of Novel Selenite Esters

The reaction of the SeO2/H2O2 system with long-chain olefinic compounds was investigated. The products sequence is epoxides → selenite esters → vicinal diols (threo diastereomers). Structure elucidation of the novel selenite esters by NMR studies including 77Se-NMR and lanthanide shift experiments showed that they are a mixture of cis/trans isomers. The SeO2/H2O2 system thus presents a novel possibility for the synthesis of selenites.